Leaving Liverpool is rarely a good decision for any footballer. Why would you willingly give up the chance of playing for one of the biggest clubs in the world?

Nevertheless, it is a choice many decide to make, with plenty left to rue the consequences.

There are few who that applies to more than Jermaine Pennant, who failed to kick on after a good first season at Anfield in 2006/07, and who has now admitted that pushing to leave after falling out of Rafa Benitez’s starting XI was the worst decision he ever made.

If Alexander Isak and Cody Gakpo miss Man City, who are you starting in their place? Would you make any other changes to the team too? 👀

Neither of them were spotted in training after picking up suspected injuries on international duty…

Jermaine Pennant regrets his Liverpool exit

Pennant never hit the heights of his first season at Liverpool, when he started – and played exceptionally well – during the 2007 Champions League final.

Injury disrupted his progress, and he did not feature anything like as much during his second season, despite a strong start, before a falling out with Benitez saw him shipped out on loan to Portsmouth in January 2009.

Still aged just 26 at the time, Pennant could easily have stayed at Liverpool for years to come, and when asked by a fan on TikTok to name the biggest regret of his career, he delved a little deeper into why he wishes that he had.

“My biggest regret? There’s quite a few of them! But I think leaving Liverpool in the manner I did,” he said. “First year was absolutely unbelievable, Champions League final, and I had a stress fracture and then I struggled to get back in the team after that.”

“Rather than working hard, have a good head, have a good attitude, professionalism, I did the opposite and that was a pattern of me throughout my career. When things weren’t going well I would kind of go off the rails and fall out with managers, and then once you do that you kind of get shifted out of the door.

“So, that’s my biggest regret, not getting my head down, working hard, trying to get back in the team and staying at Liverpool rather than leaving the way I did.

“My boyhood team who I supported as a kid and always supported and still support to this day. If I could have nailed that one down, and that is my biggest regret.”

After leaving Liverpool Pennant was never able to hit the heights expected of him during the early days of his career. A stint in Spain with Real Zaragoza did not go to plan, before he ended up back in England with Stoke City. Had he knuckled down and found a new level of professionalism to stay at Liverpool, though, things could have been very different indeed.